A rapper and pop artist train to beat Justin Timberlake up Mount Kilimanjaro—and save lives in the process

Leave it to the misfits to change the world. Kenna's voice is one of pop music's gorgeous instruments, as evidenced on two critically acclaimed if modest-selling albums, New Sacred Cow and Make Sure They See My Face. (In his book Blink, Malcolm Gladwell wondered whether the music biz was ready for the Ethiopian-born, Virginia-raised singer, whose sound channels '80s Brit synth-pop.) Kenna himself is after bigger game, assembling a team of pop star friends and other influential adventurers to climb Mount Kilimanjaro this fall to raise money and awareness for the worldwide water crisis. He's enlisted Justin Timberlake and rapper Lupe Fiasco, who has built a high-profile career from a dizzyingly eclectic collection of materials—urban noir, science fiction, Nietzsche—always taking care to bite the hip-hop hand that feeds him. (From his album The Cool, check out "Superstar" and "Dumb It Down"—"You'll sell more records if you dumb it down.") Here, Kenna and Lupe talk high-minded activism mixed with, as the Brits might say, a bit of fraternal piss-taking.

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ELLE: Kenna, I guess the idea for this climb began with you because you climbed Kilimanjaro a few years ago. How did that experience morph into this project?

KENNA: I did the first climb to kick-start my record [Make Sure They See My Face]. I was allergic to anti-altitude medicine that I took, and I didn't get to the top. So obviously I already had a vendetta with the mountain. Then after the record came out, I was in this mind-set: I can't wait until I have a giant stage to talk about important things. My dad almost died as a child from water-borne diseases in Ethiopia, and he had talked to me about digging a well in Ethiopia and I thought, I have too many friends and great people in my life that would be concerned with this subject of clean water. Maybe I can help out. When I mentioned it to Lupe, I didn't have to beat you up, did I?

LUPE FIASCO: No, no, no.

ELLE: Lupe, how did you find your way into this, besides the fact that you and Kenna are friends?

LF: Well, I'm an adventure junkie, so that was part of it—the motivation of beating Kenna to the top. Sabotaging his tent, taking the lining out of his coat, lacing it with like ants or something like that. K: Wow. Is this what's it's gonna be like? OK...

ELLE: Well, Lupe, I'd say you want to make sure you have access to those altitude-sickness pills.

LF: But seriously, I always try to be a champion of social change and anything that brings awareness to a really dire situation.

K: Beating my ass and saving people's lives...

ELLE: Lupe, a lot of your raps are about inner-city America, but you do have that track "Little Weapons," about the African kid who needs to kill a few more people before his commander will buy him a soccer ball.

LF: Yeah. I'm ingrained in a lot of—almost too many—causes and struggles around the world because that's where I come from. And the struggles haven't changed since I found out about them when I was five or six years old. They might switch a country or a leader, or this rebel group becomes passé and here comes another. And I know Kenna has a lot of other things after this climb, like, "Let's go hang-gliding for civil rights in Botswana or something."

K: I'm pretty calculated about how I approach pretty much everything in my life, and in this case, the idea was to pull together people who have pull, who I believe are influencers, on and off the stage or a movie or television set. They shape the opinions of the world.

ELLE: One of the team members is Justin Timberlake, who you've opened for in concert.

K: We met when he first came to Virginia to work on his Justified album about eight years ago and we've been friends ever since. He brings awareness but also a level of integrity. Beyond that, he went on a trip a while ago and ended up in Tanzania at a place where they had dug a well and everyone was celebrating this water and he was dumbfounded. From that day forward, water became a really big issue for Justin. He's approaching this climb with the same kind of fervor that we are. He's spending a lot of time training. We've done VO2 testing together. And at the same time, he has such a massive fan base and if he says, "Pay attention," they will. He's been a pop-culture architect for such a long time. It all adds up.

ELLE: Have you been on training runs with him?

K: I refuse because he's way more trained than I am. I'm training right now but in secret.

ELLE: Lupe, you've got a pretty intense martial arts background. Do you figure that's going to help you on the mountain?

ELLE: OK, back to the climb and the cause behind it. A cynic might ask why not just donate to a nonprofit, why go on a climb?

K: This is a personal sacrifice for people you don't know. That's a much bigger statement than a check. And don't get me wrong, we're all involved financially. But the currency of the people climbing the mountain is definitely their ability to bring eyeballs to the subject. It's a real misconception that water is a problem in Africa only. It's also an issue in Nepal, in Honduras, and in the United States of America. If we don't start paying attention now and curb our use and stop taking it for granted, we're going to be in a bad place, like everyone else.

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ELLE: How does the climb and the publicity it gets translate to more clean water in Ethiopia and wherever else?

K: It's a step-by-step process. After raising awareness about water conservation, the second step is placing money with nonprofit groups like PlayPumps that are working on solutions in the third world. We need to make sure that the wells that are put in are sustainable and people can use them for a long period of time. It starts with water. The kid who doesn't get to go to school because he's looking for water around his neck of the woods, that kid doesn't learn about HIV and then dies from AIDS. Or cholera or whatever. It all links back.

ELLE: Lupe, how did you and Kenna become friends? You're perceived as being in very different musical boxes.

LF: I think it was a duel, like with pistols.

K: Over a girl. He shot me.

ELLE: Was there actually a woman involved?

LF: No, actually there wasn't a duel. No woman either. I think we first met in a recording studio in L.A. via our accomplished mutual friend Pharrell Williams. Kenna may have been there, or not.

K: I come in "virtually." A hologram.

LF: We had a meeting of the minds. We were interested in a lot of things, and it went from there. I'm a huge fan of Kenna's music.

K: And vice versa.

LF: It's a super fan-boy relationship...

K: It's a mutual admiration society...

ELLE: A mutual interruption society?

K: Yes.

LF: One of those relationships where the gears connect, like in the past. Not to get super-astral-projectiony on you, but I knew he and I grew up in the same kind of atmosphere. So it's like we've known each other our whole lives.

ELLE: From an outside perspective, it seems that both of you are square pegs who take some pride in not fitting in commercially. Kenna, you're from an Ethiopian family with a sound that reminds people of 1980s British synth-pop. Lupe, you're building a successful hip-hop career, but a lot of your lyrics are deeply critical of hip-hop culture and you're already talking about retiring in a few years.

K: We're both contrarians.

LF: I think that's what it is. The rewards we get by being those weird guys going against the grain to me are way more massive than selling a million billion records. I like climbing mountains or going on undersea dives for whales and stuff like that.

K: At the end of the day, you can only do so many concerts and videos and movies. It comes down to who you've decided to ally with and what you've decided to accomplish together that benefits the world.

ELLE: The other theme that comes out in both your lives is the importance of fathers, so it's not only what you do but where you come from. Lupe, you've talked about growing up in West Chicago, your dad walking over to the crack house next door, armed, to let the residents know they would not be expanding the operation. You backed him up with your own piece.

LF: Yeah, my own little piece. My father had been in the military and he was a weapons specialist, so he had an affinity for weapons but also for the discipline of it. He taught us how to shoot when we were young. He opened up karate schools in the worst parts of the city, on purpose, and then he would systematically clean out a three-block radius, all of the gang-bangers and drug dealers and everybody of nefarious character. He'd scare 'em out with a gun and tough talk, and as a matter of fact, some of those people became his most powerful students. It's those underground accolades that I got to see. That's success.

ELLE: There's a lot of hard-core urban experience in Lupe's life and his raps. Does that material resonate with you?

K: I lived in lower-income neighborhoods in the inner city. Across the street were dark parts of the world. I've experienced the gamut, from third world to inner city to my parents working their way out of being secretaries and janitors to professors and real-estate people. They've shown me a path of perseverance and hard work in a peaceable way. My dad's mission for me has always been to be a man they would write about, somebody that can be respected in the world.

ELLE: There's a biting critique of mass culture and social conditions that drives a lot of Lupe's music. But Kenna, your music strikes me as more personal, more romantic, more inward.

K: I've always felt like my music would stand for itself and I would stand for myself. So I've kept my music a little bit esoteric, and I've kept the lyrics a little aloof. I try to say something important, but I don't necessarily preach. And I'm not necessarily preaching now. I'm just saying, "Here's a problem. I know what I'm going to do about it. What are you going to do about it?"